Top Siena Day Trips
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Bonnie_S, Nov 2025
A day in Chianti, Siena & San Gimigniano
The tour was very well organized and managed by Sandro who led the group through the history of this part of the Chianti region. He was very knowledgeable & pleasant.
The lunch was delicious & accompanied by tasting of 2 types of Chianti wine & a vin Santo.
Lucia, the guide to the Siena cathedral, was excellent & very thorough
Janet_B, Nov 2025
Highlight tour of Tuscany
Guiliana is an expert guide, making our trip so interesting. She is an absolute rock star! She knew so much history about the area and answered any questions we had. The views through the winding roads on our trip to Pienza and Montepulciano were spectacular. After stopping for a cappuccino in a little town along the way, we were able to explore Pienza. It rained during our time there, but we made the best of it by having a delicious lunch at a nearby cheese farm, Podere Il Casale. We were served various cheeses to try from mild to very strong, salad, and a pasta dish. Perfect. We also learned about the differences of olive oil. With our bellies full, we headed to wine tasting at the Gattevecchi winery. We were given a tour of their wine cellar, too. Even though it was raining really hard, we still managed to walk through the town of Montepulciano. This tour is a must if you want to learn more about the Tuscany region. Be sure to ask for Guiliana as your guide!
Sharon_S, Oct 2025
Wonderful tour that hits many highlights of culture, history, and art.
We learned about many of the unique traditions of Sienna and its "animal" neighborhoods, along with wonderful tidbits about the cathedral and the Duomo. 2 hours was a perfect amount of time for us, and gave us a wonderful overview of the beautiful and long history of Siena and its people. Claudia is a learned and upbeat guide and a proud lifelong resident of the city. Go, Unicorns!
Sara_B, Oct 2025
Great trip to San Gimignano & Volterra!
Guglielmo was a wonderful guide for this trip, so full of enthusiasm for the history of this area of Tuscany. He even slipped in a visit to the third hilltop town of Monteriggioni! His personal stories added a valuable dimension to the trip, and I could feel the care he put into each experience we had: visit to an impressive family winery for lunch, visit to an 83 year old sculptor of alabaster in Volterra, and “the best” gelato in San Gimignano (saffron with orange zest and almonds!).
I highly recommend this tour!
Christine_D, Sep 2025
Book this tour!!!
I cannot imagine a better tour guide than Elio. He took the time to shape the tour around our interests. It was far more than we hoped for. Elio gave us insight into the Basilica, the contrade, and even shared his expertise in Tuscan wines. He has a command of history, religion, art history, and Siena culture. We had the most excellent morning seeing Siena through his eyes.
Janice_K, Sep 2025
Excellent wine tour
If you are looking for an all-day wine tour that visits more than one winery this is a great option. The tour stops at three wineries. The first two were my favorite. The second tour included an excellent lunch. Our driver/host was knowledgeable and explained the pyramid of wines and we traveled. He was very courteous and gave the group options on how long we wanted to stay.
Laura_D, Sep 2025
Our guide, Dace, was...
Our guide, Dace, was incredibly knowledgeable about her city. She tailored the itinerary to our interests based on our questions, comments, and reactions, and she made our experience in Siena so much better than it would have been without her guidance. She even took us off the typical route to see her cantrada’s fountain & horse stall because of our interest in the snails! At the end of the tour, she looked over our short list of restaurants for lunch and helped us pick a fantastic option. Thank you, Dace!
Janice_F, Sep 2025
Wonderful evening with excellent performances.
Acoustics were wonderful. Singers and pianist were excellent, very expressive. A small facility but the staff were very well organized. Our seats were easily identified with our name. A good selection and mixture of songs. Loved the evening experience.
savitha_s, Aug 2025
Lovely wine tasting right outside Siena
It was lovely. I missed my scheduled time (11:30am) - caution getting a taxi from Siena can be challenging- so I joined the 4pm tasting. Our host Maya was great. Funny, honest and clearly passionate about what she does. My group was friendly. Wine was delicious. I told myself I wouldn’t buy wine but I ended up buying 2 bottles! Lovely dinner. Recommend to anyone!
Smokey_Y, Jul 2025
Great Class
I have had cooking classes on several international trips to include a previous to Italy and trips to Morocco and Spain. All were great experiences but this was hands down the best. The food was great but the multi-lingual aspect along with cultural insights made it truly memorable.
Donna_W, Jun 2025
Great Tour for sightseeing and wine tasting
Great tour. The castles and the wineries were great. A lot of different wines to taste, but also gained knowledge of the region and the winemaking process. Just one warning. If you get car sick easily, make sure you bring your remedy. The roads are curvy and bumpy.
Allan_B, Jun 2025
Enrich your stay at Siena
Susanne was excellent! Gave the right amount of information on the history, culture, traditions and of course food in the region. A gentle pace walking around some of the amazing streets in this living museum city. The Duomo certainly stands out Definitely enriched our stay.
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Thanks to its prime location in central Tuscany, Siena is an ideal base for exploring the wider region. Siena day trips cover a range of destinations—from the medieval hill towns of San Gimignano and Monteriggioni to the wine capitals of Montepulciano and Montalcino—and save you the hassle of piecing together tricky logistics yourself. Relax with private transport and experience the best of Chianti and the Val d’Orcia, focusing on the villages and castles or sipping your way through the region’s wineries. You can even channel the dolce vita vibe with a classic Vespa or vintage Fiat 500 excursion.
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